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Cheap flights from New York to Chicago from $186

NYC — CHI
10 Oct — 17 Oct1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 81 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago

Mon 5/1013:30 -
1 stop12h 15m
Mon 12/1020:11 -
1 stop27h 51m
Deal found 6/9$332
Wed 18/1122:14 -
1 stop11h 42m
Fri 20/1117:26 -
1 stop6h 03m
Deal found 6/9$368
Wed 30/907:17 -
Nonstop2h 43m
Thu 1/1021:35 -
Nonstop2h 22m
Deal found 9/9$370
Tue 15/913:30 -
1 stop7h 59m
Wed 16/915:50 -
1 stop8h 11m
Deal found 7/9$371
Thu 19/1111:35 -
1 stop8h 10m
Fri 20/1117:26 -
1 stop6h 03m
Deal found 6/9$382
Wed 7/1011:10 -
Nonstop2h 44m
Thu 8/1005:00 -
Nonstop2h 12m
Deal found 9/9$389
Tue 29/908:00 -
Nonstop2h 45m
Thu 1/1005:00 -
Nonstop2h 12m
Deal found 9/9$390
Sat 17/1010:47 -
Nonstop2h 48m
Wed 21/1006:43 -
Nonstop2h 23m
Deal found 7/9$393
Mon 28/906:00 -
Nonstop2h 42m
Fri 2/1016:00 -
Nonstop2h 30m
Deal found 9/9$396
Tue 6/1009:40 -
1 stop4h 19m
Tue 6/1017:29 -
1 stop4h 47m
Deal found 10/9$397
Mon 5/1020:40 -
Nonstop2h 48m
Tue 6/1021:35 -
Nonstop2h 22m
Deal found 7/9$401
Sat 12/922:29 -
1 stop11h 51m
Mon 21/910:26 -
1 stop9h 58m
Deal found 9/9$407

Find flight deals from New York to Chicago

Round-trip from

$332

One-way from

$186

Popular in

July

Cheapest in

January

Average price

$400

Good one-way deal

$171 or less
Frontier
  • Frontier
  • 5/10-12/10
  • 2 total stops
  • 40h 06m total
  • New York to Chicago
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United Airlines
  • United Airlines
  • 21/10-31/12
  • Nonstop
  • 2h 48m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($106 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average return price).
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Average for round-trip flights in September 2026
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Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from New York to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest return flight

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 14/12

19:00-23:52

1 stop5h 52m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$199

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Thu 12/11

06:00-10:25

1 stop5h 25m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$199
Fastest return journey

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sat 3/10

13:08-14:45

Nonstop2h 37m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$206

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Wed 6/1

10:00-11:50

Nonstop2h 50m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$217

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sun 27/12

07:07-09:00

Nonstop2h 53m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$241

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Tue 29/9

10:22-12:00

Nonstop2h 38m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$241

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Fri 20/11

16:45-18:30

Nonstop2h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$241

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 14/12

10:00-11:47

Nonstop2h 47m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$241

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Thu 12/11

09:00-10:48

Nonstop2h 48m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$241

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 21/9

19:14-21:00

Nonstop2h 46m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$260

Flights are sorted by cheapest return flights first.

Deals found on 9/9

Showing 1-10 of 23 resultsSorted by cheapest first
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

What is the cheapest month to book a flight from New York to Chicago?

Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $264). Flying from New York to Chicago in July is currently the most expensive (average of $478). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 86% versus a flight in the afternoon.

Weekly flight availability from New York to Chicago

The most flights from NYC to CHI are scheduled on a Tuesday (193 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (55 on average).

How much does it cost for a return flight from New York to Chicago?

Airfare is typical for this route at the moment.
New York to Chicago flights typically cost between $318 and $514 in October.
The cheapest return price found within the last 5 days was $332 on Frontier (5 Oct–12 Oct).

How often are flights from New York to Chicago delayed?

About 19% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 152 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

How far ahead should I book a flight from New York to Chicago?

The best time to book flights from New York to Chicago is 37 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Related info for your journey

  • How long is the flight from New York to Chicago?

    Airlines like United Airlines and Delta fly from New York to Chicago in about 2h 36m. The time it takes to get you to your destination can typically vary by up to 2h 49m. New York and Chicago are separated by a distance of 1152 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Malaysia Airlines (77%), GOL (76%), Air Europa (75%).

  • What are the cheapest flights from New York to Chicago?

    The cheapest flight price from New York to Chicago is $171. On average you can expect to pay $238. The most popular route, (Newark - Chicago O'Hare Intl), can usually be booked for $570.

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $264). Flying from New York to Chicago in July is currently the most expensive (average of $478). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for New York to Chicago

Newark to O'Hare Intl flights

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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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